Disclaimer: I do not own Hannah Montana or any other Disney Channel shows. If
I did then the shows would be a lot dirtier. However I love the way they pick
their female stars. My next 6-7 stories will probably be about Disney channel
girls. Also I doubt any of this has ever happened but if so then please fill
me in or send a video, or better yet send these girls over to my place
For the purposes of this story I am ignoring Miley being Hannah Montana. I
just don't know how I would work it in. May bring it up later but I doubt it.
If you like this story please send me a review. Actually even if you don't
like it send me a review. May have to wait a while for Part 2. I always have
had trouble doing anything unless I have a deadline. I started this fic a
month ago and had 3 weeks between when I started it and when I finished it.
The more reviews the faster I will write this though so please review. I am
currently planning on this being 4-5 chapters but I will need help on part 5
when i get there.
Email any suggestions or comments at: [email protected]
Hannah Montana: Cheerleader Tryouts Part 1 (Mf,M-mast,bribery,oral,voy)
I am 28 years old and currently working as a gym teacher. I am an all right
looking guy. Just under 6 foot. Brown hair and brown eyes. A little chunky
but I was also pretty muscular due to all the sports I play. My involvement
in sports was part of the reason I had gotten this job. This was my first
year and by some weird turn of events I became the cheerleading coach.
Two 14 year-old girls Miley and her best friend Lily were trying out for
cheerleading. It was late Friday afternoon and we were the only ones in the
gym. There was only one spot left and they knew that they had to go all out
to get it. I was the only judge and I was starting to have some trouble
hiding my ever-present erection. They were both knockouts and the fact that
I was twice their age did nothing to quench my thirst for some teen pussy.
Miley had beautiful long thin legs and a relatively small chest. Her brown
curly was very sweaty after the workout she had gone through and it just
added to her attraction. Lily had a slighty bigger rack with an incredible
round ass. Her legs weren't as long or skinny as Miley's but I liked that
she had more meat on her. Her blond hair was pulld back into a ponytail.
They had both been pretty good but I had basically made up my mind that
Miley was going to win this. Lily had made a few small errors when running
her routine and her voice wasn't quite loud enough. I think they both knew
the competition was already over. Lily looked pretty dejected and Miley was
trying to console her. There was only one part left before they were done
for the day.
Technically I was supposed to go home and use the weekend to make my
decision. But I was not expecting to think too hard about this decision.
Although I knew I would be running this competition over and over again in
my mind so I could release the tension I had built up recently.
The only part left was for one girl at a time to perform for me inside my
office. I wanted to see how they could do with smaller spaces and this way I
could focus on one at a time. The office was pretty incredible for a gym
teacher's office. The room was huge and had a semiprivate bathroom. There was
a female gym teacher that had an office just as big and was also linked to
the bathroom. I knew I was doing pretty well at this school and I had to be
careful to not blow it by revealing to the girls that they were turning me
I was feeling pretty strained by watching their tryout for hours. I was
planning on waiting until we were all done so I could masturbate in the
luxury of my own home. Then I realized I would have to spend the next hour
watching them perform their own routines which I knew would be even sexier
then their earlier routines. There was no way I could wait another hour
before I released. I knew that the girls would be focused on their routines
and I could probably pop one off without their knowing. As I already said I
knew I had to be careful because if I was caught my career was essentially
Miley was first and she was looking unbelievable in this short skirt that
barely made it to her thighs. She was also wearing a tube top that was giving
me a great view of her budding breasts. Can you now see why I decided to stop
trying to accomplish the impossible task of keeping my erection down?
As she started her routine I unzipped my pants and started stroking my meat.
I was doing my best to stay quiet but I am sure some noises came out. Miley
didn't seem to notice however so I kept it up. Too damn soon the music
stopped and Miley stopped dancing. I quickly stopped masturbating and cleared
"Great job Miley, you did incredible today. I will make my decision over the
weekend and tell you my answer on Monday. I'll be here from 10-2 tomorrow if
you have any questions."
"Thanks Mr. Fineberg, see you Monday."
I told her to send Lily in. As soon as Lily came in I remembered that Miley's
CD was still in the stereo. I asked Lily if Miley was still out there.
"No Mr. Fineberg. I told her to go home and I would meet her at her house
I briefly wondered why Lily had sent Miley away but figured it wasn't
"Okay. Can you give her CD back to her then?"
"So let's see this dance."
Lily put her cd in the stereo and started her routine. I unzipped again and
resumed masturbating. Lily was wearing an even shorter skirt then Miley and
a plain white t-shirt which had became transparent after sweating so much so
I could see her plain white bra. Plus with that short skirt I kept seeing
her thong panties and her tight round ass. I knew I wouldnt last long with
inspiration like this. However after only a minute Lily stopped dancing and
turned off the stereo. I was a little pissed about being stopped when I was
so close but figured as soon as I got home I could finish off.
"So did you cum yet?"
I nearly fell out of my chair.
"What are you talking about?"
"Oh come on, we saw your erection when me and Miley were dancing and I know
I heard you jacking off under your desk."
All that was running through my head was that I was never going to work
again. My entire career was flushed down the toilet after only a few years.
When I came out of my funk I noticed Lily was kneeling in front of my chair.
"What are you doing?"
"Making sure I win this competition."
Lily grabbed my dick which I never got around to putting back into my pants.
"Wow not bad, about 7-8 inches?"
"This will be a lot of fun then."
She lowered her head and started taking me into her mouth. I could feel her
tongue working on my cock the entire time and it was incredible. It had just
started and I already knew this would be the best blowjob of my life. Of
course the fact that I had been watching two gorgeous teenage girls dancing
for the last few hours would have made any release incredible. After only her
third head bob she had my entire dick in her throat.
"God I'm cumming!"
That just made her head faster and I released right into her throat. She
wasn't able to keep it all in her mouth and some leaked out onto her chin.
After she swallowed the cum in her throat she used her finger to get cum on
her chin into her mouth. The look on her face as she swallowed my cum was
the sexiest thing I have ever seen. The look on her face was worthy of the
final spot. But I knew I could do a lot more and if I gave up the chance to
fuck this hot jailbait ass I would hate myself forever.
"Well I'm guessing that was not your first blowjob?"
"No, it's the easiest way to get good grades. Much much easier then
"Well thank you for the best blowjob of my life. With talent like that you
must have a 4.0!"
"No, I would but some teachers are girls, and I don't eat rug nearly as well
as I give head. The female teachers usually only give me a B."
By now my dick which had started to soften was ready and raging for part 2.
But I decided to wait just a little longer. I used all my willpower to keep
my voice from cracking.
"So I know you give great head, but your dance moves still need some work."
"What, you mean I still don't get the spot?"
"Not yet but I will give you another chance."
I turned on the stereo with a remote.
"Now lets see you dance one more time. But this time I want you naked at the
end of the song."
She smiled her sexy slutty smile and got back onto her feet. As she started
dancing again I started stroking my cock again, this time in plain view of
her. Lily's routine would have fit right in at a strip club. I couldn't help
thinking she must have spent some time in a strip club at some point in her
life. Maybe not as a dancer but she clearly had been studying up on how to
dance. As she was bent down facing away from me she slid down her panties,
giving me a great view of her incredible round ass.
Lily continued dancing and the knowledge that she wasn't wearing any panties
under her skirt was making me want to jump her right there. Somehow I managed
to wait a little longer and enjoy her routine. Lily was massaging her tits
through her shirt when she reached in, unsnapped her bra, and took it off
through her right armhole. As I said her shirt was already basically
transparent so I had a pretty clear view of her decent sized breasts. They
weren't huge but they were still growing and it was obvious that she would
have a decent rack on her at some point in the future. Finally the song was
winding down and Lily quickly shed herself of her useless shirt and short
I looked her up and down in all her glory. She looked like a goddess. Her
young body still glistening from the dance. Her breasts going up and down at
a rapid rate due to her fast breathing. I had no idea that by end of the day
I would be having sex with a girl this gorgeous. After a quick thank you to
god, and a promise to go to church for the rest of my life, I told her to get
Lily walked back to the desk and climbed up. She gave me a come here motion
with her finger and when I got close enough she stuck her tongue in my mouth
in a kiss that was more then I could have ever imagined. Then I reclined in
my chair and watched an even better show then the strip dance. Lily first
stuck her finger in her mouth and wetted it down. She then took her finger
and slowly let it walk down her body. Her finger then went to the valley
between her breasts and she started teasing me by putting her hands on her
breasts and then quickly taking it away. Finally she took her wet finger and
started circling her left nipple.
Lily had her head thrown back in ecstasy as she continued to finger her
nipple. Her finger then continued its trek down her body between her legs.
She continued her teasing methods and started circling all around her pussy.
Lily finally started rubbing her clit with a slow deliberate motion. With the
first touch she let out a moan that made my entire body jump with anxiety.
Then she slipped a different finger into her pussy and started moaning even
harder. I couldn't take it anymore and stood up and initiated a kiss even
better then the last one.
I then broke the kiss off and started nibbling on her ear. I sucked on her
earlobe and lightly blew into her ear. Then I moved down and kissed her chin.
Then I went down to her neck and sucked on it for a while. It didn't hit me
til later that she would have to explain any hickies she got. Not that it
would have stopped me but I might have left a few less hickies. I kept moving
down and was soon at her bustline. I decided that with how much she teased me
I definitely needed to get some revenge. I lightly blew on her right nipple.
I gave it a test lick and started licking and sucking on it. Lily was still
fingering herself throughout this so I grabbed her hand and pulled it away
from her hot center. With my other hand I flicked her forgotten nipple. Her
nipples were somehow harder then my dick at this point. If I couldn't feel
them then I wouldn't think it was possible. I knew that I was affecting her
a lot by now. She was so close to an orgasm that she was starting to shake.
Then I moved away from her with a huge smile on my face.
"What are you doing! Get me off! I am so close!"
With all the pleasure she had already brought me I knew I had to stop teasing
and give her the orgasm of her lifetime. I brought my head down and examined
her pussy. She was definately a natural blond. She didn't shave her pubic
hair but there wasn't too much there because she was still so young. I
lowered my head down to her hot creamy center and gave her pussy a tentative
lick. It was the best thing I have ever tasted. Correction, this was the
best thing I had ever experienced. I don't think anyone could have ever
experienced something this good. I couldn't help myself and just dove into
her pussy and started eating her out like I had never eaten someone out
before. At the same time I used my nose to rub her clit and brought both
hands up to massage her breasts. I took a short break from eating her out to
look at Lily's face. I thought the look on her face after blowing me off was
sexy but the look on her face was like comparing a piece of dog shit and
filet mignon. I knew that I would never forget that look for the rest of my
"OH GOD I AM CLOSE! I AM GOING TO CUM HARDER THEN I HAVE EVER CUM BEFORE!
KEEP IT UP!"
With that motivation I buried my head back into the best place on Earth.
Disneyland be damned. After winning the Super bowl the players should go
here. It would definitely inspire the players even more. I was listening to
her moans and I knew right when she was ready to climax. There was something
that all of my former girlfriends loved that I decided to try. I took my
tongue out of her cunt and licked my way down her ass crack and got to her
anus. I licked around the anus and finally plunged my tongue in. It is a
weird taste that I don't really enjoy but it is a guaranteed orgasm so I
continue to do it every time I go down on a girl.
With that final push Lily climaxed harder then I had ever seen a girl climax.
I was glad the school was empty because with the scream she let off could be
heard throughout the building. And to think I thought her cheers weren't loud
enough! I laid back into the chair. With how much effort I put into it it
seemed like I had already ejaculated. I had almost forgotten all about my
erection when Lily grabbed it with her right hand. I was ready to finally
give this girl fucking of a lifetime. I stood up and got on the desk mounting
her. I was about to penetrate her when I remembered I didn't have a condom.
Lily saw my hesitation.
"Don't worry, I am on the pill."
With nothing holding me back I was ready to finally penetrate her. I inched
my dick into the tightest pussy I had ever felt. With all of her experience
I couldn't believe she was this tight. I was starting to think me and Lily
had some kind of connection. Once again she seemed to know exactly what I was
"I said I gave all my teachers head to get good grades. I've only had sex
like 2-3 times. And you are the biggest dick I have ever had in my pussy."
I must admit that made me feel much better, especially about being the
biggest one to penetrate her. So with nothing holding me back I once again
was ready for the best sex ever. I lifted her right leg up to my shoulder and
started thrusting. I could only get 4 inches into her. I decided to give her
some time to adjust to my dick in her cunt. Eventually she used her hands to
lift herself up and thrust her body towards me. With that my entire 8 inches
were buried in her. I knew I would have to be careful or I would be spent in
less then a minute. With one hand I started massaging her left breast and my
other hand I started toying with her clit. She was thrusting back at me as
hard as she could and gasping in a way that was more adorable then anything
else in my life thus far.
I remembered her reaction to me tonguing her asshole so I figured maybe she
had an anal fetish. I took my hand off her breast and caressed her skin all
the way to her ass. I hadn't taken the time to touch her ass so this was my
first experience feeling it. It was much better then I had expected and I had
to spend some time squeezing her luscious behind. I thought her breasts were
exquisite but her ass was nothing less then a masterpiece. I could grope this
ass for hours and never get tired of it.
Unfortunately I realized that I was much closer to cumming then her so I had
better get to work on her. I didn't want to leave her so close to an orgasm
so I had to really step it up. I started placing one finger into her asshole.
I thought her pussy was tight but her rectum was like a vice. I knew that I
had to find a way to put my dick there somehow. There was no way I could do
it today but at some point in time i knew i would fuck this ass. I was having
trouble getting momentum now so I took my dick out and put her on her knees
and entered her doggy-style. I shoved my thumb into her asshole and she
screamed in orgasmic bliss as she came again. The feeling of her walls
closing in on my dick was too much and with my last bit of will power I
withdrew my dick and coated her tits with my cum.
I then leaned back and fell of the desk. I landed hard on my back but I was
still the happiest man in the world. Now I just have to find some way to make
this a repeat occurrence.
"Well you definitely earned that spot."
"You know that we can't do this again right? If I get caught having sex to
get something from a teacher then my entire system is ruined."
"Okay, well I hope you remember that in a few months I have to decide who
will be the next cheerleading captain. If you want that spot then you will
need to repeat this."
"Well we'll see. For now I am happy just having a spot on the squad."
Lily cleaned up in my semi-private bathroom and put her clothes back on. When
she was walking out the door I remembered the CDs.
"Don't forget your's and Miley's CDs."
All of a sudden I remembered something else, something that scared the
bejeezus out of me.
"Hey are you going to tell Miley about what we did here today?"
"Of course not, she has no idea about my plan for good grades. She still
thinks I am a virgin! Her plan is for us both to lose our virginity together
during senior prom!"
That brought an image into my head.
"Together? Do you think I can watch? Or possibly join in?"
"Haha, believe me if you could convince her to have sex with me I would let
you do whatever you want to my body."
My mission was clear, I had to convince Miley to not only have sex before
prom, but to have sex with Lily and me. I knew it would be hard but the
reward would be so worth it.
To Be Continued